p-Toluenesulfonic acid → HCID 13533254, compound

HRID 1087151Notes

Reaction equation

HRID 1087151 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:40])=[C:5]([C:21]([O:23][CH2:24]/[CH:25]=[CH:26]/[C:27]2[CH:32]=[CH:31][C:30]([O:33]C3CCCCO3)=[CH:29][CH:28]=2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CO>[CH3:1][C:2]1[NH:3][C:4]([CH3:40])=[C:5]([C:21]([O:23][CH2:24]/[CH:25]=[CH:26]/[C:27]2[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 15632018HCID 15632018, compound

Product 1

HCID 13533254HCID 13533254, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3.4 Grams of methyl 3-(4-tetrahydropyranyloxy-phenyl)2(E)-propenyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate was dissolved in 50 ml of methanol, then 0.2 g of p-toluenesulfonic acid was added to the solution and the whole mixture was stirred at a room temperature for 4 hours. The reaction mixture was neutralized by adding sodium hydrogen carbonate, and methanol was removed by evaporation. The residue thus obtained was purified by means of a silica gel column chromatography (eluent: chloroform), recrystallized from benzene-ether to yield 2 g of methyl 3-(4-hydroxyphenyl)-2(E)-propenyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate as in the form of light yellow powdery substance. Melting point: 137.5°-139° C.

Workup

  1. customwas removed by evaporation
  2. customThe residue thus obtained
  3. customwas purified by means of a silica gel column chromatography (eluent: chloroform)
  4. customrecrystallized from benzene-ether

Sources & evidence

ORD record
ord-74ba369a81a74f758f566f3a3e17e792
Source dataset
uspto-grants-1991_07
Patent number
US05034395

Reaction notes

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